# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_2013ncs0574
_database_code_depnum_ccdc_archive 'CCDC 969748'
_audit_update_record             
;
2013-10-31 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 B F4 N4 O3 Re'
_chemical_formula_sum            'C20 H20 B F4 N4 O3 Re'
_chemical_formula_weight         637.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.1861(6)
_cell_length_b                   12.2320(5)
_cell_length_c                   16.1257(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.466(7)
_cell_angle_gamma                90
_cell_volume                     2196.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14476
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       column
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.597
_shelx_estimated_absorpt_T_min   0.202
_shelx_estimated_absorpt_T_max   0.807
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            15288
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.036
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5016
_reflns_number_gt                4678
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²+2.3016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5016
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0501
_refine_ls_wR_factor_gt          0.0494
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6519(2) 0.0731(2) 0.35753(16) 0.0174(5) Uani 1 1 d . . . . .
H1 H 0.5752 0.0411 0.3436 0.021 Uiso 1 1 calc R U . . .
C2 C 0.6987(2) 0.0739(2) 0.44008(16) 0.0212(5) Uani 1 1 d . . . . .
H2 H 0.6551 0.0431 0.4821 0.025 Uiso 1 1 calc R U . . .
C3 C 0.8107(3) 0.1208(2) 0.46018(17) 0.0219(6) Uani 1 1 d . . . . .
H3 H 0.8453 0.1222 0.5163 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8714(2) 0.1656(2) 0.39703(16) 0.0178(5) Uani 1 1 d . . . . .
H4 H 0.9479 0.1984 0.4098 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8199(2) 0.1624(2) 0.31549(15) 0.0139(5) Uani 1 1 d . . . . .
C6 C 0.8761(2) 0.2095(2) 0.24454(15) 0.0142(5) Uani 1 1 d . . . . .
C7 C 0.9887(2) 0.2584(2) 0.25288(17) 0.0198(5) Uani 1 1 d . . . . .
H7 H 1.0341 0.2612 0.3057 0.024 Uiso 1 1 calc R U . . .
C8 C 1.0341(2) 0.3032(2) 0.18340(18) 0.0219(6) Uani 1 1 d . . . . .
H8 H 1.1111 0.3367 0.1879 0.026 Uiso 1 1 calc R U . . .
C9 C 0.9656(2) 0.2983(2) 0.10718(17) 0.0197(5) Uani 1 1 d . . . . .
H9 H 0.9942 0.3297 0.0589 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8548(2) 0.2468(2) 0.10263(16) 0.0164(5) Uani 1 1 d . . . . .
H10 H 0.8084 0.2429 0.0502 0.020 Uiso 1 1 calc R U . . .
C11 C 0.5884(2) 0.1215(2) 0.04877(18) 0.0166(5) Uani 1 1 d . . . . .
C12 C 0.4976(2) 0.0332(2) 0.17893(15) 0.0155(5) Uani 1 1 d . . . . .
C13 C 0.7231(2) -0.0252(2) 0.14860(15) 0.0159(5) Uani 1 1 d . . . . .
C14 C 0.4885(2) 0.2855(2) 0.24910(15) 0.0163(5) Uani 1 1 d . . . . .
H14 H 0.4707 0.2329 0.2895 0.020 Uiso 1 1 calc R U . . .
C15 C 0.5635(2) 0.3644(2) 0.14567(16) 0.0170(5) Uani 1 1 d . . . . .
H15 H 0.6088 0.3771 0.0997 0.020 Uiso 1 1 calc R U . . .
C16 C 0.4892(2) 0.4382(2) 0.17824(16) 0.0179(5) Uani 1 1 d . . . . .
H16 H 0.4729 0.5107 0.1593 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3589(2) 0.4320(2) 0.29946(16) 0.0164(5) Uani 1 1 d . . . . .
H17A H 0.2963 0.3770 0.3079 0.020 Uiso 1 1 calc R U . . .
H17B H 0.3187 0.4970 0.2730 0.020 Uiso 1 1 calc R U . . .
C18 C 0.4221(2) 0.4642(2) 0.38330(17) 0.0218(6) Uani 1 1 d . . . . .
H18A H 0.4780 0.5253 0.3757 0.026 Uiso 1 1 calc R U . . .
H18B H 0.4699 0.4015 0.4070 0.026 Uiso 1 1 calc R U . . .
C19 C 0.3320(2) 0.4989(2) 0.44414(16) 0.0226(6) Uani 1 1 d . . . . .
H19A H 0.2634 0.4474 0.4388 0.027 Uiso 1 1 calc R U . . .
H19B H 0.3711 0.4928 0.5017 0.027 Uiso 1 1 calc R U . . .
C20 C 0.2840(3) 0.6149(2) 0.4308(2) 0.0270(7) Uani 1 1 d . . . . .
H20A H 0.3468 0.6674 0.4502 0.041 Uiso 1 1 calc R U . . .
H20B H 0.2142 0.6251 0.4624 0.041 Uiso 1 1 calc R U . . .
H20C H 0.2604 0.6267 0.3714 0.041 Uiso 1 1 calc R U . . .
N1 N 0.71080(19) 0.11562(16) 0.29624(14) 0.0132(4) Uani 1 1 d . . . . .
N2 N 0.81071(17) 0.20233(17) 0.16946(13) 0.0133(4) Uani 1 1 d . . . . .
N3 N 0.56213(17) 0.26853(17) 0.19044(13) 0.0144(4) Uani 1 1 d . . . . .
N4 N 0.44254(19) 0.38680(16) 0.24383(14) 0.0153(4) Uani 1 1 d . . . . .
O1 O 0.55186(18) 0.12827(16) -0.01984(12) 0.0215(4) Uani 1 1 d . . . . .
O2 O 0.41161(16) -0.01416(16) 0.18819(12) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.77084(18) -0.10710(15) 0.14030(14) 0.0227(4) Uani 1 1 d . . . . .
F1 F 0.11580(16) 0.67599(19) 0.08397(11) 0.0411(5) Uani 1 1 d . . . . .
F2 F 0.1963(2) 0.51175(15) 0.12383(11) 0.0401(5) Uani 1 1 d . . . . .
F3 F 0.30980(16) 0.63759(16) 0.06476(12) 0.0342(4) Uani 1 1 d . . . . .
F4 F 0.25478(15) 0.66457(14) 0.19561(10) 0.0293(4) Uani 1 1 d . . . . .
Re1 Re 0.64351(2) 0.11154(2) 0.16559(2) 0.01132(4) Uani 1 1 d . . . . .
B1 B 0.2193(3) 0.6225(3) 0.1172(2) 0.0195(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.344(3) . ?
C1 C2 1.383(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.357(3) . ?
C5 C6 1.474(3) . ?
C6 N2 1.356(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 N2 1.343(3) . ?
C10 H10 0.9500 . ?
C11 O1 1.145(3) . ?
C11 Re1 1.929(3) . ?
C12 O2 1.145(3) . ?
C12 Re1 1.922(3) . ?
C13 O3 1.149(3) . ?
C13 Re1 1.926(3) . ?
C14 N3 1.329(3) . ?
C14 N4 1.341(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(4) . ?
C15 N3 1.378(3) . ?
C15 H15 0.9500 . ?
C16 N4 1.375(3) . ?
C16 H16 0.9500 . ?
C17 N4 1.465(3) . ?
C17 C18 1.517(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.532(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.525(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 Re1 2.169(2) . ?
N2 Re1 2.1710(19) . ?
N3 Re1 2.179(2) . ?
F1 B1 1.393(3) . ?
F2 B1 1.385(4) . ?
F3 B1 1.391(4) . ?
F4 B1 1.388(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.5(2) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 120.8(2) . . ?
N1 C5 C6 115.3(2) . . ?
C4 C5 C6 123.8(2) . . ?
N2 C6 C7 121.4(2) . . ?
N2 C6 C5 115.7(2) . . ?
C7 C6 C5 122.9(2) . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 118.9(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 122.5(2) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
O1 C11 Re1 177.7(2) . . ?
O2 C12 Re1 178.8(2) . . ?
O3 C13 Re1 178.5(2) . . ?
N3 C14 N4 111.1(2) . . ?
N3 C14 H14 124.5 . . ?
N4 C14 H14 124.5 . . ?
C16 C15 N3 108.9(2) . . ?
C16 C15 H15 125.6 . . ?
N3 C15 H15 125.6 . . ?
C15 C16 N4 106.5(2) . . ?
C15 C16 H16 126.8 . . ?
N4 C16 H16 126.8 . . ?
N4 C17 C18 111.9(2) . . ?
N4 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N4 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 111.3(2) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C18 114.3(2) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C5 119.2(2) . . ?
C1 N1 Re1 123.80(17) . . ?
C5 N1 Re1 116.95(17) . . ?
C10 N2 C6 118.8(2) . . ?
C10 N2 Re1 124.46(17) . . ?
C6 N2 Re1 116.65(16) . . ?
C14 N3 C15 106.2(2) . . ?
C14 N3 Re1 124.55(18) . . ?
C15 N3 Re1 128.91(17) . . ?
C14 N4 C16 107.4(2) . . ?
C14 N4 C17 125.0(2) . . ?
C16 N4 C17 127.6(2) . . ?
C12 Re1 C13 89.53(10) . . ?
C12 Re1 C11 86.85(11) . . ?
C13 Re1 C11 91.45(10) . . ?
C12 Re1 N1 97.04(9) . . ?
C13 Re1 N1 92.05(9) . . ?
C11 Re1 N1 174.78(9) . . ?
C12 Re1 N2 171.94(9) . . ?
C13 Re1 N2 92.27(9) . . ?
C11 Re1 N2 100.95(9) . . ?
N1 Re1 N2 75.05(8) . . ?
C12 Re1 N3 92.57(9) . . ?
C13 Re1 N3 176.60(9) . . ?
C11 Re1 N3 91.34(9) . . ?
N1 Re1 N3 85.04(8) . . ?
N2 Re1 N3 85.28(8) . . ?
F2 B1 F4 109.4(2) . . ?
F2 B1 F3 109.2(2) . . ?
F4 B1 F3 110.1(2) . . ?
F2 B1 F1 109.6(2) . . ?
F4 B1 F1 109.3(2) . . ?
F3 B1 F1 109.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 N1 -0.2(4) . . . . ?
C3 C4 C5 C6 178.7(2) . . . . ?
N1 C5 C6 N2 1.3(3) . . . . ?
C4 C5 C6 N2 -177.7(2) . . . . ?
N1 C5 C6 C7 -178.6(2) . . . . ?
C4 C5 C6 C7 2.4(4) . . . . ?
N2 C6 C7 C8 1.6(4) . . . . ?
C5 C6 C7 C8 -178.5(2) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
C8 C9 C10 N2 0.6(4) . . . . ?
N3 C15 C16 N4 0.3(3) . . . . ?
N4 C17 C18 C19 -173.5(2) . . . . ?
C17 C18 C19 C20 -79.0(3) . . . . ?
C2 C1 N1 C5 -0.7(4) . . . . ?
C2 C1 N1 Re1 178.0(2) . . . . ?
C4 C5 N1 C1 0.7(4) . . . . ?
C6 C5 N1 C1 -178.3(2) . . . . ?
C4 C5 N1 Re1 -178.06(18) . . . . ?
C6 C5 N1 Re1 2.9(3) . . . . ?
C9 C10 N2 C6 1.1(4) . . . . ?
C9 C10 N2 Re1 -175.88(19) . . . . ?
C7 C6 N2 C10 -2.2(4) . . . . ?
C5 C6 N2 C10 177.9(2) . . . . ?
C7 C6 N2 Re1 175.02(19) . . . . ?
C5 C6 N2 Re1 -4.9(3) . . . . ?
N4 C14 N3 C15 0.3(3) . . . . ?
N4 C14 N3 Re1 -173.27(16) . . . . ?
C16 C15 N3 C14 -0.4(3) . . . . ?
C16 C15 N3 Re1 172.81(17) . . . . ?
N3 C14 N4 C16 -0.1(3) . . . . ?
N3 C14 N4 C17 -179.6(2) . . . . ?
C15 C16 N4 C14 -0.1(3) . . . . ?
C15 C16 N4 C17 179.4(2) . . . . ?
C18 C17 N4 C14 76.8(3) . . . . ?
C18 C17 N4 C16 -102.6(3) . . . . ?

_refine_diff_density_max         0.801
_refine_diff_density_min         -1.729
_refine_diff_density_rms         0.108

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8plus
_database_code_depnum_ccdc_archive 'CCDC 990428'
_audit_update_record             
;
2014-03-06 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N3 O3 Re S, B F4, C H Cl3 '
_chemical_formula_sum            'C19 H16 B Cl3 F4 N3 O3 Re S'
_chemical_formula_weight         745.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0109(8)
_cell_length_b                   17.8468(13)
_cell_length_c                   13.4164(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.137(2)
_cell_angle_gamma                90
_cell_volume                     2459.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12939
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       column
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.411
_shelx_estimated_absorpt_T_min   0.313
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            17474
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5579
_reflns_number_gt                5222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  
'WinGX, ver.2013.3 (L.J. Farrugia, J.App.Cryst.(2012),45,849-854)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.3316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5579
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9276(3) 0.38172(16) 0.3515(3) 0.0214(6) Uani 1 1 d . . . . .
H1 H 0.9997 0.3720 0.3304 0.026 Uiso 1 1 calc R U . . .
C2 C 0.9510(3) 0.40854(18) 0.4531(3) 0.0255(7) Uani 1 1 d . . . . .
H2 H 1.0377 0.4158 0.5014 0.031 Uiso 1 1 calc R U . . .
C3 C 0.8465(3) 0.42472(19) 0.4837(3) 0.0276(7) Uani 1 1 d . . . . .
H3 H 0.8603 0.4435 0.5532 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7207(3) 0.41298(18) 0.4108(3) 0.0238(7) Uani 1 1 d . . . . .
H4 H 0.6474 0.4243 0.4297 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7037(3) 0.38453(16) 0.3102(3) 0.0177(6) Uani 1 1 d . . . . .
C6 C 0.5743(3) 0.36911(16) 0.2290(3) 0.0183(6) Uani 1 1 d . . . . .
C7 C 0.4590(3) 0.38395(17) 0.2456(3) 0.0229(6) Uani 1 1 d . . . . .
H7 H 0.4609 0.4058 0.3107 0.027 Uiso 1 1 calc R U . . .
C8 C 0.3414(3) 0.36648(18) 0.1661(3) 0.0269(7) Uani 1 1 d . . . . .
H8 H 0.2618 0.3757 0.1764 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3409(3) 0.33537(17) 0.0714(3) 0.0260(8) Uani 1 1 d . . . . .
H9 H 0.2612 0.3227 0.0161 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4589(3) 0.32293(15) 0.0585(3) 0.0228(7) Uani 1 1 d . . . . .
H10 H 0.4587 0.3022 -0.0068 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6995(3) 0.29046(17) -0.0273(3) 0.0204(6) Uani 1 1 d . . . . .
C12 C 0.9348(4) 0.32004(18) 0.1127(3) 0.0242(8) Uani 1 1 d . . . . .
C13 C 0.7528(3) 0.42573(18) 0.0594(3) 0.0208(6) Uani 1 1 d . . . . .
C14 C 0.6565(3) 0.16908(15) 0.1394(3) 0.0186(7) Uani 1 1 d . . . . .
H14 H 0.5793 0.1878 0.0866 0.022 Uiso 1 1 calc R U . . .
C15 C 0.8601(3) 0.16941(16) 0.2586(3) 0.0201(7) Uani 1 1 d . . . . .
C16 C 0.8269(3) 0.09689(19) 0.2698(3) 0.0217(6) Uani 1 1 d . . . . .
C17 C 0.9882(3) 0.20408(18) 0.3226(3) 0.0262(7) Uani 1 1 d . . . . .
H17A H 0.9786 0.2342 0.3805 0.039 Uiso 1 1 calc R U . . .
H17B H 1.0172 0.2363 0.2764 0.039 Uiso 1 1 calc R U . . .
H17C H 1.0527 0.1645 0.3531 0.039 Uiso 1 1 calc R U . . .
C18 C 0.9068(3) 0.03603(19) 0.3409(3) 0.0276(7) Uani 1 1 d . . . . .
H18A H 0.9859 0.0578 0.3932 0.041 Uiso 1 1 calc R U . . .
H18B H 0.9309 -0.0011 0.2975 0.041 Uiso 1 1 calc R U . . .
H18C H 0.8558 0.0117 0.3784 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3205(3) 0.1023(2) 0.2425(3) 0.0292(7) Uani 1 1 d . . . . .
H19 H 0.3335 0.0958 0.1730 0.035 Uiso 1 1 calc R U . . .
B4 B 0.6966(3) 0.8784(2) 0.0473(3) 0.0206(7) Uani 1 1 d . . . . .
F1 F 0.6245(3) 0.93156(13) -0.0267(2) 0.0438(6) Uani 1 1 d . . . . .
F2 F 0.7757(2) 0.83894(15) 0.0049(2) 0.0449(7) Uani 1 1 d . . . . .
F3 F 0.77240(18) 0.91355(13) 0.14278(19) 0.0347(5) Uani 1 1 d . . . . .
F4 F 0.6095(3) 0.82935(11) 0.0663(2) 0.0376(6) Uani 1 1 d . . . . .
N1 N 0.8066(2) 0.36876(13) 0.2809(2) 0.0165(5) Uani 1 1 d . . . . .
N2 N 0.5741(3) 0.33953(14) 0.1361(2) 0.0164(5) Uani 1 1 d . . . . .
N3 N 0.7609(2) 0.21067(14) 0.1823(2) 0.0173(5) Uani 1 1 d . . . . .
O1 O 0.6632(2) 0.27133(13) -0.11435(19) 0.0278(5) Uani 1 1 d . . . . .
O2 O 1.0351(3) 0.31861(15) 0.1059(3) 0.0369(7) Uani 1 1 d . . . . .
O3 O 0.7477(3) 0.48317(13) 0.0196(2) 0.0297(5) Uani 1 1 d . . . . .
Re1 Re 0.76181(2) 0.32669(2) 0.11829(2) 0.01564(7) Uani 1 1 d . . . . .
S1 S 0.66918(7) 0.07964(4) 0.18460(7) 0.02283(17) Uani 1 1 d . . . . .
Cl1 Cl 0.32170(10) 0.19807(5) 0.27064(8) 0.0414(2) Uani 1 1 d . . . . .
Cl2 Cl 0.16831(8) 0.06252(5) 0.23100(8) 0.0305(2) Uani 1 1 d . . . . .
Cl3 Cl 0.44792(8) 0.05533(5) 0.34400(8) 0.03120(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.347(4) . ?
C1 C2 1.378(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.357(4) . ?
C5 C6 1.475(4) . ?
C6 N2 1.353(4) . ?
C6 C7 1.391(4) . ?
C7 C8 1.384(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(5) . ?
C9 H9 0.9500 . ?
C10 N2 1.352(4) . ?
C10 H10 0.9500 . ?
C11 O1 1.142(4) . ?
C11 Re1 1.933(3) . ?
C12 O2 1.140(5) . ?
C12 Re1 1.937(4) . ?
C13 O3 1.148(4) . ?
C13 Re1 1.924(3) . ?
C14 N3 1.314(4) . ?
C14 S1 1.695(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(4) . ?
C15 N3 1.405(4) . ?
C15 C17 1.495(4) . ?
C16 C18 1.503(4) . ?
C16 S1 1.728(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 Cl1 1.750(4) . ?
C19 Cl2 1.774(4) . ?
C19 Cl3 1.774(4) . ?
C19 H19 1.0000 . ?
B4 F4 1.388(4) . ?
B4 F2 1.392(4) . ?
B4 F1 1.395(4) . ?
B4 F3 1.399(4) . ?
N1 Re1 2.188(3) . ?
N2 Re1 2.177(3) . ?
N3 Re1 2.243(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.7(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 C6 115.7(3) . . ?
C4 C5 C6 122.8(3) . . ?
N2 C6 C7 121.5(3) . . ?
N2 C6 C5 115.7(3) . . ?
C7 C6 C5 122.8(3) . . ?
C8 C7 C6 119.2(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N2 C10 C9 121.9(4) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
O1 C11 Re1 177.8(3) . . ?
O2 C12 Re1 176.9(4) . . ?
O3 C13 Re1 176.5(3) . . ?
N3 C14 S1 115.4(2) . . ?
N3 C14 H14 122.3 . . ?
S1 C14 H14 122.3 . . ?
C16 C15 N3 114.0(3) . . ?
C16 C15 C17 124.2(3) . . ?
N3 C15 C17 121.7(3) . . ?
C15 C16 C18 129.4(3) . . ?
C15 C16 S1 109.9(2) . . ?
C18 C16 S1 120.7(2) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Cl1 C19 Cl2 110.1(2) . . ?
Cl1 C19 Cl3 110.68(19) . . ?
Cl2 C19 Cl3 109.80(19) . . ?
Cl1 C19 H19 108.7 . . ?
Cl2 C19 H19 108.7 . . ?
Cl3 C19 H19 108.7 . . ?
F4 B4 F2 109.3(3) . . ?
F4 B4 F1 107.8(3) . . ?
F2 B4 F1 109.4(3) . . ?
F4 B4 F3 109.8(3) . . ?
F2 B4 F3 110.2(3) . . ?
F1 B4 F3 110.2(3) . . ?
C1 N1 C5 118.5(3) . . ?
C1 N1 Re1 124.8(2) . . ?
C5 N1 Re1 116.66(19) . . ?
C10 N2 C6 119.0(3) . . ?
C10 N2 Re1 123.8(3) . . ?
C6 N2 Re1 117.2(2) . . ?
C14 N3 C15 110.5(2) . . ?
C14 N3 Re1 118.5(2) . . ?
C15 N3 Re1 130.75(19) . . ?
C13 Re1 C11 86.88(13) . . ?
C13 Re1 C12 86.93(14) . . ?
C11 Re1 C12 86.35(15) . . ?
C13 Re1 N2 92.18(11) . . ?
C11 Re1 N2 98.12(12) . . ?
C12 Re1 N2 175.39(12) . . ?
C13 Re1 N1 93.08(12) . . ?
C11 Re1 N1 172.82(10) . . ?
C12 Re1 N1 100.82(13) . . ?
N2 Re1 N1 74.70(10) . . ?
C13 Re1 N3 176.97(10) . . ?
C11 Re1 N3 91.68(11) . . ?
C12 Re1 N3 95.64(12) . . ?
N2 Re1 N3 85.39(9) . . ?
N1 Re1 N3 88.02(9) . . ?
C14 S1 C16 90.14(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -1.6(5) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 N1 -0.8(5) . . . . ?
C3 C4 C5 C6 178.8(3) . . . . ?
N1 C5 C6 N2 1.5(4) . . . . ?
C4 C5 C6 N2 -178.2(3) . . . . ?
N1 C5 C6 C7 -178.3(3) . . . . ?
C4 C5 C6 C7 2.0(5) . . . . ?
N2 C6 C7 C8 1.5(5) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C6 C7 C8 C9 -0.7(5) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 N2 0.8(5) . . . . ?
N3 C15 C16 C18 178.8(3) . . . . ?
C17 C15 C16 C18 -2.9(6) . . . . ?
N3 C15 C16 S1 -0.3(4) . . . . ?
C17 C15 C16 S1 178.0(3) . . . . ?
C2 C1 N1 C5 1.7(4) . . . . ?
C2 C1 N1 Re1 179.8(2) . . . . ?
C4 C5 N1 C1 -0.4(4) . . . . ?
C6 C5 N1 C1 179.9(3) . . . . ?
C4 C5 N1 Re1 -178.7(2) . . . . ?
C6 C5 N1 Re1 1.7(3) . . . . ?
C9 C10 N2 C6 0.0(4) . . . . ?
C9 C10 N2 Re1 -176.8(2) . . . . ?
C7 C6 N2 C10 -1.1(4) . . . . ?
C5 C6 N2 C10 179.1(3) . . . . ?
C7 C6 N2 Re1 175.9(2) . . . . ?
C5 C6 N2 Re1 -3.9(3) . . . . ?
S1 C14 N3 C15 -0.6(4) . . . . ?
S1 C14 N3 Re1 174.60(15) . . . . ?
C16 C15 N3 C14 0.6(4) . . . . ?
C17 C15 N3 C14 -177.7(3) . . . . ?
C16 C15 N3 Re1 -173.8(2) . . . . ?
C17 C15 N3 Re1 7.8(5) . . . . ?
N3 C14 S1 C16 0.4(3) . . . . ?
C15 C16 S1 C14 0.0(3) . . . . ?
C18 C16 S1 C14 -179.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 F3 0.95 2.52 3.326(4) 143.2 2_745
C2 H2 F2 0.95 2.50 3.113(4) 122.5 2_745
C2 H2 Cl2 0.95 2.92 3.669(3) 136.9 4_666
C7 H7 F4 0.95 2.47 3.043(4) 118.6 2_645
C10 H10 F4 0.95 2.51 3.138(4) 124.1 3_665
C10 H10 Cl1 0.95 2.82 3.624(4) 143.1 4_565
C14 H14 F4 0.95 2.36 3.219(4) 151.0 3_665
C18 H18C O3 0.98 2.58 3.459(4) 149.8 4_566
C19 H19 F1 1.00 2.23 3.222(5) 173.0 3_665
C19 H19 F2 1.00 2.54 3.272(5) 130.2 3_665

_refine_diff_density_max         1.993
_refine_diff_density_min         -1.637
_refine_diff_density_rms         0.162

_shelxl_version_number           2014-1

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9plus_a
_database_code_depnum_ccdc_archive 'CCDC 990429'
_audit_update_record             
;
2014-03-06 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O4 Re S, C F3 O3 S'
_chemical_formula_sum            'C20 H17 F3 N3 O7 Re S2'
_chemical_formula_weight         718.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   12.1102(9)
_cell_length_b                   13.1182(9)
_cell_length_c                   14.8639(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2361.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5


_exptl_crystal_description       prism
_exptl_crystal_colour            'pale Yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.022
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.394
_shelx_estimated_absorpt_T_min   0.564
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            18399
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.668
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5408
_reflns_number_gt                5329
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  
'WinGX, ver.2013.3 (L.J. Farrugia, J.App.Cryst.(2012),45,849-854)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+6.3332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2312 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.371(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5408
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 1.0211(6) 1.0062(5) 0.6652(5) 0.0259(15) Uani 1 1 d . . . . .
C13 C 0.8952(6) 0.9434(5) 0.5234(5) 0.0237(13) Uani 1 1 d . . . . .
C12 C 0.8053(6) 1.0106(6) 0.6788(5) 0.0294(16) Uani 1 1 d . . . . .
C10 C 1.1216(5) 0.7737(5) 0.6165(4) 0.0226(13) Uani 1 1 d . . . . .
H10 H 1.1583 0.8372 0.6236 0.027 Uiso 1 1 calc R U . . .
C9 C 1.1845(6) 0.6869(6) 0.6046(5) 0.0251(14) Uani 1 1 d . . . . .
H9 H 1.2628 0.6903 0.6047 0.030 Uiso 1 1 calc R U . . .
C8 C 1.1309(5) 0.5949(7) 0.5926(5) 0.0279(13) Uani 1 1 d . . . . .
H8 H 1.1721 0.5340 0.5842 0.033 Uiso 1 1 calc R U . . .
C7 C 1.0170(5) 0.5923(7) 0.5928(5) 0.0261(13) Uani 1 1 d . . . . .
H7 H 0.9791 0.5298 0.5836 0.031 Uiso 1 1 calc R U . . .
C6 C 0.9583(5) 0.6819(5) 0.6066(4) 0.0209(13) Uani 1 1 d . . . . .
C5 C 0.8365(5) 0.6853(5) 0.6085(4) 0.0211(13) Uani 1 1 d . . . . .
C4 C 0.7701(6) 0.6008(6) 0.5931(5) 0.0267(13) Uani 1 1 d . . . . .
H4 H 0.8028 0.5363 0.5817 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6559(6) 0.6107(6) 0.5942(5) 0.0294(15) Uani 1 1 d . . . . .
H3 H 0.6096 0.5532 0.5846 0.035 Uiso 1 1 calc R U . . .
C2 C 0.6111(5) 0.7061(6) 0.6098(5) 0.0255(13) Uani 1 1 d . . . . .
H2 H 0.5334 0.7155 0.6101 0.031 Uiso 1 1 calc R U . . .
C1 C 0.6812(6) 0.7878(6) 0.6251(4) 0.0246(14) Uani 1 1 d . . . . .
H1 H 0.6500 0.8532 0.6355 0.030 Uiso 1 1 calc R U . . .
C14 C 1.0325(6) 0.8338(5) 0.8194(5) 0.0246(13) Uani 1 1 d . . . . .
H14 H 1.0962 0.8437 0.7832 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8543(5) 0.8285(5) 0.8557(5) 0.0232(12) Uani 1 1 d . . . . .
C16 C 0.8987(6) 0.8022(5) 0.9362(4) 0.0225(12) Uani 1 1 d . . . . .
C17 C 0.7331(6) 0.8363(6) 0.8377(5) 0.0294(15) Uani 1 1 d . . . . .
H17A H 0.6926 0.8342 0.8947 0.044 Uiso 1 1 calc R U . . .
H17B H 0.7098 0.7790 0.7997 0.044 Uiso 1 1 calc R U . . .
H17C H 0.7174 0.9006 0.8067 0.044 Uiso 1 1 calc R U . . .
C18 C 0.8424(6) 0.7760(6) 1.0232(5) 0.0296(15) Uani 1 1 d . . . . .
H18A H 0.7648 0.7994 1.0205 0.036 Uiso 1 1 calc R U . . .
H18B H 0.8792 0.8132 1.0728 0.036 Uiso 1 1 calc R U . . .
C19 C 0.8440(6) 0.6630(6) 1.0441(6) 0.0330(16) Uani 1 1 d . . . . .
H19A H 0.8018 0.6500 1.1000 0.040 Uiso 1 1 calc R U . . .
H19B H 0.8078 0.6251 0.9946 0.040 Uiso 1 1 calc R U . . .
C20 C 0.5738(7) 0.5237(6) 0.8473(6) 0.0355(16) Uani 1 1 d . . . . .
N2 N 1.0107(4) 0.7719(4) 0.6183(4) 0.0199(11) Uani 1 1 d . . . . .
N1 N 0.7920(5) 0.7781(4) 0.6259(4) 0.0199(11) Uani 1 1 d . . . . .
N3 N 0.9313(5) 0.8479(4) 0.7882(4) 0.0231(12) Uani 1 1 d . . . . .
O1 O 1.0860(5) 1.0686(4) 0.6755(4) 0.0331(11) Uani 1 1 d . . . . .
O3 O 0.8855(4) 0.9646(4) 0.4496(3) 0.0306(11) Uani 1 1 d . . . . .
O2 O 0.7456(5) 1.0757(4) 0.6956(4) 0.0361(13) Uani 1 1 d . . . . .
O4 O 0.9529(5) 0.6274(5) 1.0547(4) 0.0425(15) Uani 1 1 d . . . . .
H4A H 0.9713 0.6320 1.1091 0.064 Uiso 1 1 calc R U . . .
O5 O 0.7152(4) 0.4163(4) 0.7572(3) 0.0324(11) Uani 1 1 d . . . . .
O6 O 0.5205(4) 0.3745(5) 0.7445(4) 0.0380(14) Uani 1 1 d . . . . .
O7 O 0.6179(4) 0.3383(4) 0.8835(4) 0.0354(12) Uani 1 1 d . . . . .
F1 F 0.6523(5) 0.5597(5) 0.9020(5) 0.0623(17) Uani 1 1 d . . . . .
F2 F 0.5567(6) 0.5916(5) 0.7833(4) 0.0657(18) Uani 1 1 d . . . . .
F3 F 0.4806(4) 0.5178(4) 0.8957(3) 0.0417(11) Uani 1 1 d . . . . .
S1 S 1.04079(14) 0.79728(14) 0.92761(11) 0.0255(3) Uani 1 1 d . . . . .
S2 S 0.61169(12) 0.39903(15) 0.80289(11) 0.0259(3) Uani 1 1 d . . . . .
Re1 Re 0.90787(2) 0.90367(2) 0.64773(2) 0.01887(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 O1 1.144(9) . ?
C11 Re1 1.938(7) . ?
C13 O3 1.138(8) . ?
C13 Re1 1.926(7) . ?
C12 O2 1.146(9) . ?
C12 Re1 1.930(8) . ?
C10 N2 1.344(9) . ?
C10 C9 1.381(10) . ?
C10 H10 0.9500 . ?
C9 C8 1.381(11) . ?
C9 H9 0.9500 . ?
C8 C7 1.380(9) . ?
C8 H8 0.9500 . ?
C7 C6 1.389(10) . ?
C7 H7 0.9500 . ?
C6 N2 1.352(9) . ?
C6 C5 1.475(9) . ?
C5 N1 1.356(9) . ?
C5 C4 1.389(10) . ?
C4 C3 1.389(9) . ?
C4 H4 0.9500 . ?
C3 C2 1.384(11) . ?
C3 H3 0.9500 . ?
C2 C1 1.386(10) . ?
C2 H2 0.9500 . ?
C1 N1 1.348(8) . ?
C1 H1 0.9500 . ?
C14 N3 1.324(9) . ?
C14 S1 1.681(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.356(10) . ?
C15 N3 1.393(9) . ?
C15 C17 1.496(9) . ?
C16 C18 1.503(9) . ?
C16 S1 1.726(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.515(11) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O4 1.407(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 F2 1.320(10) . ?
C20 F1 1.337(10) . ?
C20 F3 1.340(9) . ?
C20 S2 1.823(8) . ?
N2 Re1 2.174(5) . ?
N1 Re1 2.188(5) . ?
N3 Re1 2.231(6) . ?
O4 H4A 0.8400 . ?
O5 S2 1.444(5) . ?
O6 S2 1.441(6) . ?
O7 S2 1.441(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C11 Re1 178.3(6) . . ?
O3 C13 Re1 178.0(6) . . ?
O2 C12 Re1 178.2(7) . . ?
N2 C10 C9 122.6(7) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C8 C9 C10 118.6(6) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C7 C8 C9 119.4(8) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C7 C6 119.4(8) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
N2 C6 C7 121.2(6) . . ?
N2 C6 C5 116.1(6) . . ?
C7 C6 C5 122.7(6) . . ?
N1 C5 C4 121.1(6) . . ?
N1 C5 C6 115.4(6) . . ?
C4 C5 C6 123.5(6) . . ?
C5 C4 C3 120.1(7) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 C4 118.4(7) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N1 C1 C2 122.5(7) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
N3 C14 S1 115.5(5) . . ?
N3 C14 H14 122.3 . . ?
S1 C14 H14 122.3 . . ?
C16 C15 N3 114.6(6) . . ?
C16 C15 C17 124.4(6) . . ?
N3 C15 C17 121.0(6) . . ?
C15 C16 C18 129.6(6) . . ?
C15 C16 S1 109.9(5) . . ?
C18 C16 S1 120.5(5) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 113.2(6) . . ?
C16 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C16 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
O4 C19 C18 111.1(6) . . ?
O4 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
O4 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
F2 C20 F1 108.1(7) . . ?
F2 C20 F3 107.1(7) . . ?
F1 C20 F3 107.1(7) . . ?
F2 C20 S2 112.6(6) . . ?
F1 C20 S2 111.0(6) . . ?
F3 C20 S2 110.7(5) . . ?
C10 N2 C6 118.8(6) . . ?
C10 N2 Re1 124.2(5) . . ?
C6 N2 Re1 116.8(4) . . ?
C1 N1 C5 118.7(6) . . ?
C1 N1 Re1 124.6(5) . . ?
C5 N1 Re1 116.7(4) . . ?
C14 N3 C15 110.0(6) . . ?
C14 N3 Re1 119.4(5) . . ?
C15 N3 Re1 130.5(4) . . ?
C19 O4 H4A 109.5 . . ?
C14 S1 C16 90.0(3) . . ?
O7 S2 O6 114.7(4) . . ?
O7 S2 O5 115.6(3) . . ?
O6 S2 O5 114.6(3) . . ?
O7 S2 C20 102.0(4) . . ?
O6 S2 C20 103.0(4) . . ?
O5 S2 C20 104.4(4) . . ?
C13 Re1 C12 88.9(3) . . ?
C13 Re1 C11 89.8(3) . . ?
C12 Re1 C11 85.3(3) . . ?
C13 Re1 N2 93.9(2) . . ?
C12 Re1 N2 174.0(3) . . ?
C11 Re1 N2 100.0(2) . . ?
C13 Re1 N1 90.6(2) . . ?
C12 Re1 N1 99.8(3) . . ?
C11 Re1 N1 174.9(3) . . ?
N2 Re1 N1 74.9(2) . . ?
C13 Re1 N3 175.5(3) . . ?
C12 Re1 N3 95.5(3) . . ?
C11 Re1 N3 90.7(2) . . ?
N2 Re1 N3 81.6(2) . . ?
N1 Re1 N3 88.5(2) . . ?

_refine_diff_density_max         1.212
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.097

_shelxl_version_number           2014-1

